In my opinion, Winnipeg is the coldest, smallest, poorest city in the NHL. Winnipeg is part of Canada which is a disadvantage to players seeking money since with all things equal, we are not able to offer the great corporate support since our market is the smallest, therefore endorsements are not going to be as high, we get the smallest exposure and quite frankly we are a hugely underestimated market. We generate great revenue as a team but we have only 1 good thing going and that is passionate fans.
Winnipeg/Atlanta has the worst playoff performance in that the Winnipeg Jets v 1.0 made it to the 2nd round twice and never won a game past round 1, Atlanta Thrashers were worse, therefore, many players have no hope for Winnipeg making it far in the playoffs. We haven't even made the playoffs since relocating and have never been a top the standings. Players NTC will see less of Winnipeg when this team becomes a powerhouse. Players do want to go to winners and a winning culture. Detroit has been great at that.
I don't see Winnipeg ever being a destination city for NHLer's until Canadian hockey players take pride and we see someone like Jonathan Toews come to Winnipeg to play at home. It is common in other sports, however, in hockey the pride just doesn't seem to be there.